"There's a certain shared life experience that is tough for someone else who's not in this industry to kind of wrap their head around," Evans explains. "Letting someone go to work with someone for three months and they won't see them. It really, it certainly puts the relationship to the test."

Long before he was Captain America and dating A-list actresses, Evans was an intern in New York City, and, according to him, it was the best of times, it was worst of times. "I know I'm going to L.A. in August," he tells the magazine of that period in his life. "So I go home and that spring I would wake up around noon, saunter into high school just to see my buddies, and we'd go get high in the parking lot. I just f**ked off."

"I lost my virginity that year," he adds. "1999 was one of the best years of my life."

Esquire

Esquire

Esquire

Later that year, Evans was caught off guard when his parents announced they were divorcing. "In my own life, I have a deep connection with my family and the value of those bonds," he confides. "If something goes south with a friend, you have the option to say we're not friends anymore. Your family -- that's your family."

Continuing to walk down memory lane, Evans also shares an embarrassing story about first meeting fellow Massachusetts native Ben Affleck, when he came in for a meeting about Gone Baby Gone. "First thing I say to him: 'Am I going to be okay where I parked?' He was like, 'Where did you park?' I said, 'At a meter.' And he was like, 'Did you put money in the meter?' And I said, 'Yep.' And he says, 'Well, I think you'll be okay,'" he recounts. "I was like, 'This is off to a great f**king start.'"